Insecticidal composition of pyrethrum and a methylene dioxyphenyl synergist



Patented De '30, 1947 InsEc'rIcmAL' COMPOSITION OF PYRETH- I I RUM AND A METHYLENE moxrrnnm SYNERGIST I Martin E. Synerhoim, Hastings on Hudson, N. 1 a

assignor to Boyce Thompson Institute for Plant N Research, Inc., a corporation of New York No Drawing. 1 Application Augusta, 1944,

Serial No. 547,984

names 0 C H=C-C N uHs e-Phenyl-fi-(3,4methylenedioxyphenyl) acrylonitrile (2) ago a-Phenyl-fi-(SA-methylenedioxypbenyl) N-cyclohexylscrylamide CHr-C a mOyano-B-(3,i-methylenedioxyphenyl) N-cyclohexylacrylamide which are exceptional synergistic agents in compositions comprising pyrethrin in a spray me dium, advantageously a mutual solvent. Spray compositions comprising one or more of the 'compounds and pyrethrin in a hydrocarbon or mineral Oil, such as odorless kerosene or naphtha, are especially effective insecticides.

The aforementioned condensation products increase the toxic effect of pyrethrin to a very marked extent and when they are incorporated in a suitable spraying medium with pyrethrin the resulting composition has more killing effect against such insects as the ordinary housefly than Y benzyl cyanide in the presence of alkali as de- 5 hexylamide is not new, though the cyclohexylamide is new. The acid has been described by Bodrous, Compt. Rend. Acad. Sci. (Paris), 153:350-351 (1911). The compound represented by Formula 2 may be prepared by condensing piperonal with the alkali salt of phenyl acetic acid in the presence of acetic anhydride and pyridine, followed by conversion of the acid formed to the N-cyclohexyl amide by well known methods for preparing amides.

The acid of which compound 3 is the cyclohexyl amide has been, described in Beilsteins Handbuch der organischen Chemie. 4 Aufl, Bd. 19, p. 288; Julius Springer, Berlin 1934. The condensation of piperonal with methyl cyanoacetate in the presence of sodium ethylate with subsequent conversion to the cyclohexyl amide may be used to prepare compound 3.

The synergistic efiect of the compounds is shown in' the following tables in which the results were obtained by the Standard Feet-Grady method with five-day Old files as described on pages 92 to 98 of "Pyrethrum flowers, by C. B.

the combined effects of the pyrethrin and the compound when used alone. The invention provides an improved insecticidal composition comprising one or more compounds of the group consisting of (1) a-phenyl-,8-(3,4-methylenedioxyphenyl) acrylonitrile, (2) a-phenyl-fi-(3A-methylenedioxyphenyl) N-cyclohexylacrylamide, and (3) a-cyano-p-(3,4-methy1enedioxyphenyl) N- cyclohexylacrylamide and pyrenthrin in a liquid spray medium,.for example, of hydrocarbon char- Gnadinger, 1936 edition, with compositions comprisin the compounds and 0,025 gm. pyrethrin per 100 ml. of odorless kerosene:

Table I O'll' Per Per Cent Grams 1' Per Cent Com ound Cent Adjusted P 100 m Kill Km Km Table 11 G. r G.pyretluins Per Cent 0'1"! Per Cmpmmd ml. per 100 ml. K Pent Kill a) 0.5 0.025 88 51 0. 5 0.00 30 67 (2) 0. 5 0.025 91 51 0. 5 0. O0 74 51 (3) 0.5 0.025 96 51 0.5 0.00 65 Pyrcthrins alone 0. 025 19 is I be prepared by-heating together piperonai with 55 Less than 22- Iciaim: 1. An insecticidal composition comprising pyrothrin and a. compound of the group consisting oi' a-phenyi-p-i3,4-methyienedioxyphenyl) acryionitriie. u-phenyi-p (3,4-methyienedioxyphenyl) 5 N-cyciohexylacryiamide, and -cysn ,-fi- (3,4- methyienedioxyphenyi) N-cyclohexyiacryiamide. 2. An insecticidal composition according to claim 1 in which the compound and pyrethitin n're disssoived in kerosene. I

3. An insecticidal composition according to claim 1 in which the compound and-'pyrethrin are dissolved in a mineral-oil base solvent.- 7

4. An insecticidal composition according to mar'nnnncns 0mm The foiiowihcxeferences are of record in the tile 01' this patent:

UNITED STATES PATENTS I,

\ Date Number I Name 2,326,350 Gertler et a1. Aug. 10, 1943 2,335,384 Bousquet Nov. 30, 1943 10 2,362,128 Gertler et a1. Nov. 7,.1944

OTHER REFERENCES Synerholm et aL, Contributions from Boyce Thompson Institute, v01. .14, No. 2, 1945, pages claim 1 inwhich the compound and pyrethrin are 15 79-89.- dissoiveci in naphtha. Y p 4 i MARI'IN E. SYNERHOLM.

Rom-k et ai., Chemical and Engineering News,

Sept. 10, 1944, page 1457. (Copy in Library.) 

